Chapter 14 Carboxylic Acids
Multiple Choice
1. Which is the IUPAC name for the following compound? (Sec. 14.3)
O
C
H3C
a)
b)
c)
d)
O
CH2 CH2 CH2 C OH
2-oxohexanoic acid
5-oxohexanoic acid
methyl butyroxo ketone
4-ketopentanoic acid
2. Which is the correct structure for Z-3-hexenedioic acid? (Sec. 14.3)
O
O
CH2COH
a)
H C
H
H
b)
HOCH2C
CH2COH
C
C
CH2COH
H
O
O
O
O
H
c)
H
COH
C CH2COH
C
H
d)
CH2COH
H
O
COH
O
3. Which is the IUPAC name for the following compound? (Sec. 14.3)
H
C
H
C
COH
O
a)
b)
c)
d)
E-3-phenylpropenoic acid
Z-3-carboxy-1-phenylethene
E-1-phenylpropenoic acid
Z-benzylacrylic acid
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Chapter 14 Carboxylic Acids
4. Which is the structure for potassium hydrogen oxalate? (Sec. 14.3)
O
O
CO K
CO K
a)
CH2
b)
CH2 4
c)
COH
O
O
O
5. Which structures are correctly named (common name)? (Sec. 14.3)
O
O
CH3COH
I
formic acid
H2C
CHCOH
II
acrylic acid
O
COH
CH2
COH
O
III
malonic acid
a)
b)
c)
d)
CO K
CO K
COH
COH
O
O
O
COH
COH
O
IV
succinic acid
I, II
II, III
III, IV
II, IV
162
d)
COH
O
Chapter 14 Carboxylic Acids
6. Arrange the compounds in order of increasing solubility in water (least soluble first). (Sec. 14.4)
O
O
HOC CH2 CH2 CH3
K OC CH2 CH2 CH3
I
II
O
O
HOC CH3
HOC
III
a)
b)
c)
d)
IV
II, III, I, IV
IV, I, III, II
I, IV, II, III
II, III, I, IV
7. Arrange the compounds in order of increasing order of solubility in water (least soluble first).
(Sec. 14.4)
O
O
O
COH
CO K
COH
8.
C
C
CO K
CO K
COH
O
O
O
I
a)
b)
c)
d)
O
II
III
O
O
IV
IV, III, I, II
I, III, II, IV
IV, II, III, I
I, II, III, IV
Which compounds are soluble in water? (Sec. 14.4)
O
O
HOC CH2 CH3
I
a)
b)
c)
d)
HOCH2CH2CH3
II
H3C
C
III
I, II, IV
I, III, IV
I, II, III
II, III, IV
163
CH3
CH3CH2CH3
IV
Chapter 14 Carboxylic Acids
9. Arrange the compounds in order of increasing boiling point (lowest first). (Sec. 14.4)
O
CH3
O
O
C OH
COH
CO Na
C
CH3
H
II
I
a)
b)
c)
d)
III
IV
II, I, III, IV
I, II, III, IV
III, I, II, IV
IV, I, II, III
10. Arrange the compounds in order of increasing boiling point (lowest first). (Sec. 14.4)
O
O
O
HOCCH2CH2COH
O
HOCCH2CH2CH3
I
HOCCH2CH2CH2CH2CH3
II
a)
b)
c)
d)
O
HOCCH2CH2CH2CH2COH
IV
III
I, II, III, IV
IV, II, II, I
II, III, I, IV
I, II, IV, III
11. Arrange the compounds in order of increasing acidity (lowest first). (Sec. 14.5)
CH3
Cl
Cl
C COH
CH2CH2COH
Cl
H O
I
a)
b)
c)
d)
CH3
O
C COH
O
CH3CH2COH
Cl O
II
III
IV, I, II, III
III, II, IV, I
IV, II, I, III
II, I, III, IV
164
O
IV
Chapter 14 Carboxylic Acids
12. Arrange the compounds in order of increasing acidity (lowest first). (Sec. 14.5)
OH O
COH
H3C C
H
I
a)
b)
c)
d)
CH3CH2
O
O
COH
C OH
O
Cl
IV
III
II
III, II, I, IV
I, II, IV, III
II, III, I, IV
II, I, III, IV
13. Arrange the compounds in order of increasing acidity (lowest first). (Sec. 14.5)
O
O
O
O
COH
COH
COH
COH
CH3
NO2
III
IV
Cl
I
a)
b)
c)
d)
II
IV, I, III, II
III, II, I, IV
II, III, I, IV
III, II, IV, I
165
CH2
COH
Chapter 14 Carboxylic Acids
14. Which reactions proceed nearly to completion as written? (Sec. 14.5)
O
I.
O
CH3COH + NaOH
CH3CO Na
O
II.
CH3COH +
Na2CO3
CH3CO Na
CH3COH +
NaHSO4
CH3CO Na
O
H2CO3
+
H2SO4
CH3CO Na
I, II
III, IV
I, III
II, IV
15. Which mixtures can be separated by treatment with aqueous NaOH? (Sec. 14.5)
O
OH
CH2OH
COH
CH2COH
and
I
II
O
COH
a)
b)
c)
d)
O
and
O
CH2OH
O
O
CO Na
CH3COH +
a)
b)
c)
d)
+
O
O
IV.
H2O
O
O
III.
+
COH
OH
and
and
III
IV
I, II
III, IV
II, IV
I, III
166
+
COH
Chapter 14 Carboxylic Acids
16. Which reactions yield the same carboxylic acid? (Sec. 13.10)
O
I.
K2Cr2O7
CH2CH
II.
CH2CH2Br
III.
CH2CH3
H2SO4
+ Mg
KMnO4
ether
CO2
H3O
OH
IV.
a)
b)
c)
d)
CH2OH
K2Cr2O7
H2SO4
I, II
III, IV
II, IV
I, III
17. Which compounds undergo thermal decarboxylation? (Sec. 14.9)
O
O
COH
COH
I.
II.
COH
COH
O
O
O
O
O COH
III.
C
C CH3
CH2COH
IV.
CH3
a)
b)
c)
d)
O
I, II
II, III
III, IV
II, IV
167
H 3O
Chapter 14 Carboxylic Acids
18. Which conditions are best for the transformation? (Sec. 14.6)
O
O
O
a)
b)
c)
d)
HO
COH
COH
LiAlH4
NaBH4
Ag(NH3)2OH / NH4OH
Pyridine . Cr3O4
19. Which conditions are best for making the following compound? (Sec. 14.7)
O
CH3
C
OCH2CH2CH3
O
a)
CH3OH
+
CH3CH2COH
O
b) CH3COH
+
HCl
O
+
CH3CH2COH
+ HCl
O
c)
CH3COH
+ CH3CH2CH2OH + HCl
O
d) CH3CH2CH2O Na + CH3COH
20. The following compound is prepared by Fischer esterification of which combination of reagents?
(Sec. 14.7)
O
COCH3
COCH3
O
a)
b)
c)
d)
1,2-dihydroxybenzene and methanol
salicylic acid and methanol
phthalic acid and methanol
benzoic acid and methanol
168
Chapter 14 Carboxylic Acids
21. Which compound is prepared by reaction of benzoic acid with ammonia and water? (Sec. 14.5)
O
C
O
C
NH2
O
CO
O NH4
CH2NH2
NH3
a)
b)
c)
d)
22. Which conditions will convert pentanoic acid to pentanoyl chloride? (Sec. 14.8)
a)
b)
c)
d)
HCl
NaCl
SOCl2
LiAlH4 followed by HCl
23. Acetophenone (methyl phenyl ketone) is the product from thermal degradation of which compound?
(Sec. 14.7)
O
O
COH
CH2 C H
O
O
COH
CCH2COH
O
C CCH3
CH2CCH2COH
H O
COH
O
a)
b)
d)
c)
24. A mixture of the following compounds was extracted in the order 1) 1 M HCl, 2) 1 M NaOH, 3) ether.
Which compound is extracted into the basic layer? (Sec. 14.5)
O
NH2
COH
O
C
I
a)
b)
c)
d)
II
III
I
II
III
All of the above
169
O
CH3
Chapter 14 Carboxylic Acids
25. A mixture of the following compounds was extracted in the order 1) 1 M HCl, 2) 1 M NaOH, 3) ether.
Which compound is extracted into the ether layer? (Sec. 14.5)
O
COH
NH2
O
C
I
a)
b)
c)
d)
II
CH3
III
I
II
III
All of the above
Fill in the Blank
The IUPAC name of the following structure is ___________________________. (Sec. 14.3)
O
OH
2. The IUPAC name of the following structure is ___________________________. (Sec. 14.3)
O
O
OH
3. The major product that completes the following reaction is,
O
1) LiAlH4, ether
OH
2)H2O
(Sec. 14.6)
170
Chapter 14 Carboxylic Acids
4. The reagents that complete the following reaction are,
O
O
OH
O
OH
OH (Sec. 14.6)
5. The major product that completes the following reaction is,
O
OH
OH
H+
(Sec. 14.7)
6. The reagents that complete the following reaction are,
O
O
Cl
OH
(Sec. 14.8)
7. The major product that completes the following reaction is,
O
O
heat
OH
(Sec. 14.9)
8. The reagents that complete the following reaction are,
O
O
OH
O
(Sec. 14.7)
171
Chapter 14 Carboxylic Acids
9. The reagents that complete the following reaction are,
O
O
OH
OH
(Sec. 14.6)
10. Complete the following reaction mechanism for the Fisher esterification of acetic acid. (Sec. 14.7)
O
+O H
H+
OH
OH
H+
OH
+ OCH3
H
OH
HOCH3
OH
+O H
O
OCH3
+
OH2
OCH3
OCH3
True-False
1. The order of acidity of the following carboxylic acids is,
O
O
Cl
OH
>
OH
O
>
O
OH
Cl
>
Cl
OH
(Sec. 14.5)
2. The order of acidity of the following carboxylic acids is,
Cl
Cl
O
O
OH >
Cl
Cl
O
O
OH
>
Cl
Cl
(Sec. 14.5)
172
OH
>
OH
Chapter 14 Carboxylic Acids
3. The order of acidity of the following carboxylic acids is,
O
Cl
>
OH
F
O
O
O
>
> Br
OH
OH
OH
(Sec. 14.5)
4. The name of the following compound is 2,2-dibromopropanedioic acid. (Sec. 14.3)
O
O
Br
Br
HO
OH
5. The order of boiling points for the following compounds is,
O
OH
>
O
OH >
>
O
(Sec. 14.4)
6. The structure of Z-2-butendioic acid is,
O
OH
HO
O
(Sec. 14.3)
7. The product of heating 4-oxopentanoic acid is butanone and carbon dioxide. (Sec. 14.9)
8. The product of the reaction of hexanoic acid and chromic acid is hexanol. (Sec. 13.10)
9. The product of the reaction of benzoic acid and sodium hydroxide is sodium benzoate. (Sec. 14.5)
10. The product of the reaction of acetic acid and thionyl chloride is acetyl chloride. (Sec. 14.8)
173
Chapter 14 Carboxylic Acids
Answers
Multiple Choice
1. b
2. c
3. a
4. c
5. b
6. b
7. a
8. c
9. d
10. c
11. c
12. c
13. b
14. a
15. d
16. b
17. b
18. b
19. c
20. c
21. b
22. c
23. b
24. b
25. c
Fill in the Blank
1. 2,4-cyclopentadiene carboxylic acid
2. 2,2-dimethyl-3-oxobutanoic acid
3.
OH
4. 1) NaBH4, ethanol, 2) H2O
5.
O
O
6. SOCl2
7.
O
CH3
8. phenol, H+
174
Chapter 14 Carboxylic Acids
9. Pt, H2
10.
O
H+
OH
+O H
OH
H+
OH
+ OCH3
H
OH
HOCH3
OH
+O H
O
OCH3
+
OH2
OCH3
OCH3
True-False
1. F
2. T
3. F
4. T
5. F
6. F
7. F
8. F
9. F
10. T
175